Dreaming of flying first-class, lounging in luxury hotels, or planning your perfect vacation without breaking the bank? What if you could unlock the secrets to doing it all with points and miles you’re already earning — or could be?
In this episode of The Agent of Wealth Podcast, host Marc Bautis is joined by Elliot Rosenberg, Founder of Hack My Honeymoon, to uncover the secrets of turning everyday spending into nearly-free luxury travel. Elliot, an expert in helping high-spenders and business owners maximize the value of their credit card points, shares how he helps clients go beyond 2% cash back to achieving 10-20% in rewards toward unforgettable experiences.
From premium flights to five-star accommodations, Elliot reveals his strategies for optimizing points, earning bonuses, and making the most of your travel rewards to create memories that last a lifetime.
In this episode, you will learn:
- How to strategically earn and redeem credit card points for luxury travel experiences.
- The importance of using the right cards for specific spending categories to maximize rewards.
- Why flexibility in your travel plans can significantly enhance the value of your points.
- Common mistakes people make when attempting to travel hack (and how to avoid them).
- Tips for extracting maximum value from premium credit cards with high annual fees.
- And more!
Resources:
hackmyhoneymoon.com | Elliot Rosenberg on Social: @EHRosenberg | Bautis Financial: 8 Hillside Ave, Suite LL1 Montclair, New Jersey 07042 (862) 205-5000 | Schedule an Introductory Call
Disclosure: The transcript below has been edited for clarity and content. It is not a direct transcription of the full episode, which can be listened to above.
Welcome back to The Agent of Wealth Podcast, this is your host Marc Bautis. Today, we’ve diving into a topic that combines smart financial strategies with the thrill of travel – credit card hacks. For many, credit cards are just a tool for convenience or basic rewards, but what if you could unlock tens of thousands of dollars in value, luxury vacations, and life-changing experiences?
Joining us is someone who has mastered this game: Elliot Rosenberg, Founder of Hack My Honeymoon. Elliot specializes in helping high-spenders and business owners get maximum value from credit card points. Instead of 2% cash-back, he can help people get 10-20% back toward nearly-free luxury travel.
Today, Elliot will share his journey, his strategies, and explain how you can maximize your rewards and turn them into unforgettable memories. Elliot, welcome to the show!
Thanks for having me, Marc. I’m excited to be here.
So, what inspired you to dive into travel hacking and turn it into your profession?
I had another travel business over 10 years ago in Brazil. We were helping people have culturally immersive experiences in Rio de Janeiro’s favelas — communities that often have a bad reputation but are rich in hospitality, warmth, and vitality. Most travelers to Brazil never see these realities because of the stigma.
We facilitated stays with families in these communities, offering travelers authentic, immersive experiences while generating sustainable income for the families hosting them. It was like Airbnb, but a much higher-touch version. In the process, I found myself envious of my customers. Many were traveling around the world, waking up to new adventures every day, while I was stationary — even if it was in an amazing place.
Eventually, I handed over that business to a new team and embarked on a 15-month backpacking journey through 17 countries in Asia. I was 24 or 25 at the time, didn’t have much money, and wanted to take a big trip while I had the freedom to do so. That’s when I discovered the power of credit card points and miles. Used responsibly, they can generate tens of thousands of dollars in nearly free travel. That trip was my first big exposure to the potential of points and miles, and I’ve been hooked ever since.
Over time, friends and family started asking me how they could do the same. A few years ago, people began asking for help planning their honeymoons. Weddings are so expensive, and often the only tangible outcomes are a big bill, a video, and some photos. I realized you could leverage wedding expenses to create something truly memorable — luxury travel for less than the cost of economy.
Since then, I’ve focused on helping business owners and high spenders — newlyweds or not — turn their business and personal spending into luxury travel at about 90% off the cash rate.
Can you walk us through an example? Let’s say I want to plan a honeymoon or big trip. What are the key aspects of planning from a travel hacking perspective?
We often work with high spenders who already use credit cards but aren’t maximizing their rewards. Most people only see a 1-2% return, whether it’s cash back or miles. For example, someone who flies Delta may open a Delta credit card to earn SkyMiles.
However, by optimizing your spending and using the right cards, you can achieve a 10% return toward luxury travel — like business and first-class flights, five-star resorts, and more. It’s about earning rewards strategically and then using them effectively.
Booking the trip is where people often struggle. Knowing the best way to use your points and miles can dramatically increase their value.
Are there specific credit cards that work best for this? And how do you help individuals or couples through the process?
We offer a luxury points travel concierge service that handles everything for you. The main thing you’ll need to do is open new credit cards if that’s one of our recommendations. For instance, if you spend a lot on dining and groceries, we might suggest the American Express Gold Card, which offers 4x points per dollar in those categories.
Once you’ve accumulated points — many clients come to us with points they’ve already earned — we’ll work with you to clarify the following:
- What are your travel goals and preferences?
- What are your non-negotiables for the trip?
- What are your travel constraints?
From there, we build a full itinerary. Typically, this includes business or first-class flights outside the U.S. and stays at luxury hotels costing $500–$2,000+ per night, all using points.
I’ve seen cards that offer 2-5% back, whether in cash or points. But you mentioned 10% or even 20% returns. That’s a significant leap. How is that achievable?
It’s a combination of earning points at higher rates — by using cards aligned with your spending categories — and redeeming them for maximum value. Categories could include dining, groceries, software, cloud services, or office supplies, depending on your business and personal expenses.
Many people redeem their points through travel portals like Amex or Chase at a rate of 1 cent per point. But big banks often have airline and hotel loyalty program partners. For example, one Amex or Chase point can typically be transferred to an airline or hotel program at a 1:1 ratio.
By transferring your points strategically, you can unlock far greater value. For instance, a business-class flight from JFK to Paris on Air France might cost $4,000–$5,000. Booking through a travel portal would require around 400,000 points. However, transferring those points to Air France or British Airways and redeeming them strategically might only cost 100,000–150,000 points.
So if I just do the quick math on this — and I know we’re using examples and high-level numbers — but if someone theoretically spends, let’s say, $10,000 a month on their Amex bill…
Sure. In your example, to get that flight that normally costs $4,000, they’d need to spend about $120,000 on the credit card in a year if they’re earning points at 1 cent per dollar. Ideally, though, you should aim for a base earning of two points per dollar — two flexible, transferable points from cards like Chase, Capital One, or Amex. Beyond that, you’d use a card with category bonuses. For example, the Amex Gold Card offers four points per dollar on dining and groceries, and the Amex Platinum Card gives five points per dollar on flights booked directly with airlines. By putting the right expenses on the right cards, your earning rate should exceed the 1-2% average. Then, when it comes time to use your points, you won’t just cash them out at a penny per point. Instead, you’ll transfer them to airlines or hotels — assuming you’re flexible.
Flexibility is key. If you say, “I need to go to London over July 4th weekend with my family of five in lie-flat business class, and we want to stay at the Park Hyatt for five nights,” it’s going to be much harder. But if you say, “I want to go somewhere warm and beachy during the cold Northeast winter, and I’m open to options within a 12-hour flight,” it becomes much easier to find great deals.
So, you’re optimizing on both sides — earning more points per dollar spent and redeeming points for greater value than you’d typically get with a credit card.
We also help people, much like a travel agent would, by finding destinations and building itineraries that align with their travel goals, preferences, and constraints.
Let’s talk practicality. Using the example of earning points for a JFK-to-Paris flight within a year, how many credit cards would someone need to open? Just at a high level — would it be a couple?
Generally, two or three credit cards will allow you to earn two to five points per dollar, which is usually sufficient for most people and business owners. Personally, I’ve opened 92 credit cards over the past 10 years. My credit score is still over 800 because I understand how credit works — but I’m not advocating that for anyone else. I do it to take advantage of signup bonuses, often closing the card after a year to avoid annual fees. For the average high spender, they don’t have the time or interest to manage that. Two, three, maybe four daily earner cards should be enough, ideally earning different types of points. Just as you, as a financial advisor, would recommend diversifying investments, I recommend diversifying points. Amex points transfer to certain partners, Chase to others, and Capital One to yet another set. By having cards from different programs and spending strategically, you can achieve excellent results.
Can someone do this repeatedly? For instance, could they start over each year?
Do you mean opening a credit card repeatedly?
Yes, or just the whole travel hacking concept. Is there a point where credit card companies or travel companies flag someone? It almost sounds too good to be true — going from earning 2-3% rewards to 10 times that. What’s the catch?
I never advocate for anything illegal, unethical, or in violation of terms and conditions set by banks or loyalty programs. However, if you open too many cards too quickly, earn a signup bonus, and then cancel the card within 12 months, it could signal to the issuer that you’re gaming the system. On the other hand, if you open two or three cards over six months and put significant spending on them — say tens of thousands of dollars — the banks are usually happy. Especially with Amex, which has high card processing fees, they earn significant revenue every time you make a purchase. For people spending hundreds of thousands of dollars annually, you’re a highly profitable customer.
Can you explain how credit card companies make money, for those who might not know?
Sure. Different banks have different models, but they earn revenue from interest fees, late fees, foreign transaction fees, and miscellaneous charges. For premium customers who pay their balance in full each month, they make money from card processing fees. This fee — often called a merchant discount rate — ranges from 2-4%, depending on the issuer and card network (Visa, Mastercard, or Amex). Amex tends to have the highest fees because they cater to a premium customer base. Merchants accept Amex despite the cost because it gives them access to high-spending customers.
Premium cards also often have annual fees, like the Amex Platinum’s $695 fee. While these cards offer benefits worth thousands of dollars, banks intentionally structure programs to make it difficult for customers to maximize those benefits, ensuring they remain profitable.
When you recommend cards to clients, are they typically premium cards with annual fees?
It depends. For non-points benefits like lounge access or loyalty status, premium cards with annual fees of a few hundred dollars may be worth it. We also help clients extract full value from these cards, ensuring the benefits outweigh the cost. For example, if someone pays $695 for an Amex Platinum Card but gets $600 back for United Flights they’d already take, it’s worth it. Often, small adjustments — like using GrubHub instead of DoorDash — can recoup these fees and more.
Some people chase high savings rates at banks, constantly moving accounts for an extra 0.25%. Is it similar with credit cards? Do clients frequently switch based on promotions, or is it more about sticking to a long-term strategy?
It’s not quite as dynamic as savings rates. The main reason to switch cards is for signup bonuses. For example, an Amex Business Platinum signup offer might yield 250,000 points after spending $20,000 in three months. Those points can translate to $10,000–$20,000 in first-class flights. But for most clients, we focus on a stable, long-term strategy. Program changes rarely happen so dramatically that you’d shift everything from one issuer to another.
What’s one of the most extravagant or unique honeymoons you’ve planned?
I once worked with a couple who flew business class, saving $8,000–$10,000 per person on round-trip flights from LA to Nairobi, Kenya, for a Maasai Mara Safari. They flew Qatar Airways Q Suite, featuring privacy doors, lie-flat beds, and the option to join two beds together. The service included champagne, Dine-on-Demand, and luxurious lounges. They also stayed at the Park Hyatt in Zanzibar, Tanzania, a stunning, historic hotel. They saved over $20,000 on their honeymoon by opening just a few cards each.
Personally, I flew first-class from JFK to Abu Dhabi for my honeymoon. The Etihad flight included a chauffeur, a suite with a couch and bed, a personal chef, and a shower at 35,000 feet. The flight was valued at $17,000, and I paid only $7 in taxes. We also stayed in an overwater bungalow in the Maldives for free — another highlight of travel hacking.
I’m sure some people think they can do this themselves. What mistakes do they make?
There are many potential pitfalls. For instance, you might transfer points to a program like British Airways, assuming you can book a specific flight, only to discover it’s unavailable or was phantom availability. Now your points are stuck in a program you can’t use.
Another mistake is spending irresponsibly — chasing points without a clear budget, which can lead to debt or a damaged credit score. This hobby requires discipline and planning. If you don’t have a handle on your spending patterns, it’s not the right approach for you.
Great tips! Elliot, thanks for joining me today and sharing your expertise. How can listeners connect with you?
You can find us at hackmyhoneymoon.com, where there’s a form to share your travel plans, points, and luxury preferences. I’m also active on social media as @EHRosenberg on most platforms, sharing daily tips and deals.
Awesome. We’ll include all that information in the resources section of the show notes. Thanks again, Elliot. And thank you to everyone who tuned into today’s episode. Don’t forget to follow The Agent of Wealth on the platform you listen from and leave us a review of the show. We are currently accepting new clients, if you’d like to schedule a 1-on-1 consultation with our advisors, please do so below.
Bautis Financial LLC is a registered investment advisor. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial advisor and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance.